15/10/2026
In 2018, I was five years into developing properties and getting pretty impressed with myself.
I had bought properties, finished projects and made good money. Things that used to intimidate me had become routine. When somebody questioned a deal, I was formulating my response while they were still talking.
That should have concerned me, but it didn't.
I think five years in can be a dangerous time for an operator. You've learned enough to feel experienced, and a few good years can make you think you've discovered fire. Naturally, it's time to sell a class and declare yourself a guru.
The problem is you don't know what you don't know. And once your head gets big enough, you're not particularly interested in finding out.
I had three painful projects around that point in my career. Berenice, Vine and Hollywood. I still think about all three.
I should have known better
I wasn't new to real estate in 2013. I was new to development. I'd already been through the 2008 housing crash, when we had to change how we acquired properties. We dug into foreclosures, learned the process and made much of our money facilitating short sales.
That experience should have taught me to be careful about assuming anything would keep working forever.
Then I started developing properties and working for a hedge fund. The experience came quickly. So did the money.
I started making decisions like the good deals would never stop.
Five years of operating in similar conditions gave me plenty of practice. It also gave me a very convenient explanation for why things were going well: I was good at this.
There were people offering opinions I should have heard. I shut them down. My head was too big to hear them.
In 2018, the hedge fund packed up and left. Their plans changed, and I had to figure out mine. Around the same time, those three projects were giving me an education I hadn't been interested in signing up for.
Vine sold in April 2018, Berenice that August and Hollywood in May 2019. Getting them sold didn't turn them into good projects.
Those projects are part of my track record. The good ones are easier to talk about, obviously. These are the ones that made me look harder at how I was making decisions.
Then the business changed again
By 2019, I was spreading things out, doing more marketing and wholesaling. I was finding other ways to generate business.
Then 2020 showed up.
When lockdown was called, lenders pulled out of my deals. Financing I was counting on disappeared, and I was back to square one.
Apparently, rebuilding the business once wasn't enough entertainment.
I leaned further into construction. That work kept me moving during lockdown. Over the years, rising rates have required more adjustments. When conventional financing made deals harder to put together, we looked harder at seller financing.
I had already changed directions several times. Somehow, I still needed reminding that the business wasn't going to settle down just because I felt experienced.
Leave room for another opinion
Early in your career, asking questions is easy. You know you need help. After some success, somebody questioning your judgment can start feeling like somebody questioning whether you belong in the business.
That's a lousy reason to dismiss a good concern.
I had to get comfortable being challenged again, especially when I was excited about a deal. If someone sees a problem, I need to let them finish explaining it before I start defending my numbers.
For an operator reading this, that's worth checking. Who can tell you a deal is a bad idea? Do you actually listen? What happens to your plan if your ARV is $100,000 less than expected or your project runs six months longer than you anticipated?
I've had plenty of reasons to ask those questions. I don't need to manufacture another one.
I still trust my experience. Part of that experience is remembering the times I got it wrong.
If you're five years in and things are going well, enjoy it. Just leave enough room in your head for somebody else's opinion.
Mine was full in 2018. Making room got expensive.
See what went wrong here: https://www.2cdchicago.com/projects
What changed the way you evaluate deals after your first few successful years?
